2,4-Dihydroxybenzaldehyde → 4-Benzyloxy-2-hydroxybenzaldehyde

HRID 2253728Notes

Reaction equation

HRID 2253728 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(=O)CC>[CH2:11]([O:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[CH:9]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 72132,4-DihydroxybenzaldehydeHCID 7498Benzyl Bromide

Product 1

HCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2,4-dihydroxybenzaldehyde (5.52 g, 0.04 mmol), benzylbromide (5.7 ml, 0.048 mmol) and K2CO4 (6.64 g) in 90 ml of 2-butanone is stirred for 48 hours at room temperature and then heated to reflux for 8 hours. After cooling to room temperature and filtering, the filtrate is concentrated in vacuo and the residue chromatographed (25% EtOAc/Hexane) to obtain 4-benzyloxy-2-hydroxybenzaldehyde which is used directly in the next step.

Workup

  1. temperatureheated
  2. temperatureto reflux for 8 hours
  3. temperatureAfter cooling to room temperature
  4. filtrationfiltering
  5. concentrationthe filtrate is concentrated in vacuo
  6. customthe residue chromatographed (25% EtOAc/Hexane)

Sources & evidence

ORD record
ord-09f6dbc5e164425992f984d37fb007dd
Source dataset
uspto-grants-1993_08
Patent number
US05232948

Reaction notes

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